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Many retirees enter their golden years anticipating a certain financial comfort, only to be blindsided by the realization that their Social Security benefits can be taxed. In fact, nearly half of retirees are shocked to learn that as much as 85% of their benefits could potentially be taxed based on their overall income. For single individuals, if your retirement income falls between $25,000 and $34,000, you can expect up to 50% of your benefits to be taxable. For those earning more, it escalates to 85%. Married couples filing jointly encounter similar thresholds.